So if I take and mp3 file at 320 kbps, and re encode to 190 kbps, do I lose more quality than if I was just going to take an original file and encode it to 190 kbps? Do you lose some quality ever time you encode? Was that clear enough?

This question has been asked a million times before, but I will answer your question anyway. MP3 is a lossy codec. Even if you rip a CD directly into MP3, you will lose some audio information. Then, if you take the resulting MP3 and encode it into some other bitrate/format, you will lose more information and so on...

That is why we have lossless audio codecs like FLAC. FLAC files store all audio information, which is why they are bigger than MP3s. So, if you are worried about sound quality, use a lossless codec like FLAC.

Sorry to ask a repetitive question...I'm new to this. So I guess there's no way to measure exactly how much information is lost? Pretty much, I'm debating whether or not take some mp3's I have at 320 kpbs and decrease them to 190 kbps to save some space.

If you want to know how much is lost that you can tell: ABX it. FooBar2000 can do this pretty easily. It all depends on how good are your ears.

The quality loss of a single transcode from 320k is negligeable IMO -- most would be hard pressed to even abx it.